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ChemicalBook CAS DataBase List N,N-DIDODECYLMETHYLAMINE
2915-90-4

N,N-DIDODECYLMETHYLAMINE synthesis

15synthesis methods
-

Yield: 55%

Reaction Conditions:

in ethanol for 48 h;Reflux;

Steps:

2.3.1 Preparation of N,N-didodecylmethylamine
3.6mL (14mmol) of 16 N-dodecylmethylamine and 6.4mL (27mmol) of 17 1-bromododecane were dissolved in 30mL of absolute 18 EtOH. The mixture was heated to reflux for two days. The solvent was removed under reduced pressure, the residue was dissolved in 19 CHCl3 and washed three times with a saturated aqueous solution of 20 NaHCO3. The organic layer was dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The oily residue was purified by chromatography on silica gel (eluent CHCl3) to afford 2.89g of 21 N,N-didodecylmethylamine (yield 55%). 1H NMR (δ CDCl3, 300MHz) ppm: 0.84 (t, 3JHH=9.18Hz, 6H, CH2CH3); 1.16-1.29 (m, 36H, NCH2CH2(CH2)9CH3); 1.54 (m, 4H, NCH2CH2); 2.34 (s, 3H, NCH3); 2.49 (m, 4H, NCH2). 13C NMR (δ CDCl3, 75MHz) ppm: 14.11; 22.69; 27.28; 27.63; 29.36; 29.64; 31.92; 42.31; 57.91

References:

Mauceri, Alessandro;Giansanti, Luisa;Bozzuto, Giuseppina;Condello, Maria;Molinari, Agnese;Galantini, Luciano;Piozzi, Antonella;Mancini, Giovanna [Biochimica et Biophysica Acta - Biomembranes,2019,vol. 1861,# 8,p. 1468 - 1475]

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